JP2008519023A5 - - Google Patents
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- JP2008519023A5 JP2008519023A5 JP2007539647A JP2007539647A JP2008519023A5 JP 2008519023 A5 JP2008519023 A5 JP 2008519023A5 JP 2007539647 A JP2007539647 A JP 2007539647A JP 2007539647 A JP2007539647 A JP 2007539647A JP 2008519023 A5 JP2008519023 A5 JP 2008519023A5
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- Japan
- Prior art keywords
- formula
- compound
- organic solvent
- reaction mixture
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- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims 18
- 239000003960 organic solvent Substances 0.000 claims 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 6
- 239000011541 reaction mixture Substances 0.000 claims 6
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 5
- LIWAQLJGPBVORC-UHFFFAOYSA-N Ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 claims 4
- 239000002585 base Substances 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 4
- 150000002825 nitriles Chemical class 0.000 claims 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N Carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 3
- 239000012044 organic layer Substances 0.000 claims 3
- 239000001184 potassium carbonate Substances 0.000 claims 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- -1 (S) -3- (1- dimethylaminoethyl) carbonyl phenol Chemical compound 0.000 claims 2
- GQZXRLWUYONVCP-MRVPVSSYSA-N 3-[(1R)-1-(dimethylamino)ethyl]phenol Chemical compound CN(C)[C@H](C)C1=CC=CC(O)=C1 GQZXRLWUYONVCP-MRVPVSSYSA-N 0.000 claims 2
- XSVMFMHYUFZWBK-NSHDSACASA-N EXELON Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 claims 2
- XZVYDRLPXWFRIS-UHFFFAOYSA-N N-ethyl-N-methylcarbamoyl chloride Chemical compound CCN(C)C(Cl)=O XZVYDRLPXWFRIS-UHFFFAOYSA-N 0.000 claims 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 238000010791 quenching Methods 0.000 claims 2
- 230000000171 quenching Effects 0.000 claims 2
- 229960004136 rivastigmine Drugs 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 1
- SYOSODBLQVBZAY-UHFFFAOYSA-N 2-[1-(dimethylamino)ethyl]phenol Chemical compound CN(C)C(C)C1=CC=CC=C1O SYOSODBLQVBZAY-UHFFFAOYSA-N 0.000 claims 1
- GQZXRLWUYONVCP-QMMMGPOBSA-N 3-[(1s)-1-(Dimethylamino)Ethyl]Phenol Chemical compound CN(C)[C@@H](C)C1=CC=CC(O)=C1 GQZXRLWUYONVCP-QMMMGPOBSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N Butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N Camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 claims 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N Propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims 1
- 229910052808 lithium carbonate Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 239000001187 sodium carbonate Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1207/MUM/2004 | 2004-11-08 | ||
| IN1207MU2004 | 2004-11-08 | ||
| PCT/IB2005/003237 WO2006048720A1 (fr) | 2004-11-08 | 2005-10-29 | Procede efficace de preparation de (s)-3-[(1-dimethyl amino)ethyl]-phenyl-n-ethyl-n-methyl-carbamate |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011259013A Division JP2012072171A (ja) | 2004-11-08 | 2011-11-28 | （ｓ）−３−［（１−ジメチルアミノ）エチル］−フェニル−ｎ−エチル−ｎ−メチル−カルバミン酸の効率的製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008519023A JP2008519023A (ja) | 2008-06-05 |
| JP2008519023A5 true JP2008519023A5 (fr) | 2008-11-27 |
| JP4954886B2 JP4954886B2 (ja) | 2012-06-20 |
Family
ID=35539313
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007539647A Expired - Fee Related JP4954886B2 (ja) | 2004-11-08 | 2005-10-29 | （ｓ）−３−［（１−ジメチルアミノ）エチル］−フェニル−ｎ−エチル−ｎ−メチル−カルバミン酸の効率的製造方法 |
| JP2011259013A Pending JP2012072171A (ja) | 2004-11-08 | 2011-11-28 | （ｓ）−３−［（１−ジメチルアミノ）エチル］−フェニル−ｎ−エチル−ｎ−メチル−カルバミン酸の効率的製造方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011259013A Pending JP2012072171A (ja) | 2004-11-08 | 2011-11-28 | （ｓ）−３−［（１−ジメチルアミノ）エチル］−フェニル−ｎ−エチル−ｎ−メチル−カルバミン酸の効率的製造方法 |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1856036B1 (fr) |
| JP (2) | JP4954886B2 (fr) |
| KR (1) | KR101168211B1 (fr) |
| ES (1) | ES2615487T3 (fr) |
| RU (1) | RU2393148C2 (fr) |
| WO (1) | WO2006048720A1 (fr) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4954886B2 (ja) * | 2004-11-08 | 2012-06-20 | エムキュア ファーマシューティカルズ リミテッド | （ｓ）−３−［（１−ジメチルアミノ）エチル］−フェニル−ｎ−エチル−ｎ−メチル−カルバミン酸の効率的製造方法 |
| ES2267399B1 (es) * | 2005-08-04 | 2008-02-01 | Ragactives, S.L. | Procedimiento para la obtencion de carbamatos de fenilo. |
| US7767843B2 (en) * | 2006-03-02 | 2010-08-03 | Apotex Pharmachem Inc. | Process for the preparation of phenylcarbamates |
| EP2054373B1 (fr) * | 2006-08-17 | 2010-06-30 | Alembic Limited | Procédé pour la préparation de rivastigmine amélioré |
| WO2008037433A1 (fr) * | 2006-09-29 | 2008-04-03 | Synthon B.V. | Procédé de fabrication de carbamates d'aminoalkylphényle et intermédiaires de cette fabrication |
| WO2008110339A2 (fr) * | 2007-03-09 | 2008-09-18 | Synthon B.V. | Polymorphes d'hydrogénotartrate de rivastigmine |
| WO2009086705A1 (fr) * | 2008-01-10 | 2009-07-16 | Shanghai Institute Of Pharmaceutical Industry | Procédé de préparation de rivastigmine, ses intermédiaires et procédé de préparation des intermédiaires |
| US8420846B2 (en) | 2008-08-25 | 2013-04-16 | Jubilant Life Sciences Limited | Process for producing (S)-3-[(1-dimethylamino)ethyl] phenyl-N-ethyl-N-methyl-carbamate via novel intermediates |
| GB0823554D0 (en) * | 2008-12-24 | 2009-01-28 | Novartis Ag | Process for the preparation of optically active compounds using transfer hydrogenation |
| CN103664702A (zh) * | 2013-12-18 | 2014-03-26 | 成都医路康医学技术服务有限公司 | 一种卡巴拉汀的生产工艺 |
| CN103664703A (zh) * | 2013-12-18 | 2014-03-26 | 成都医路康医学技术服务有限公司 | 一种酒石酸卡巴拉汀的合成工艺 |
| CN104987294B (zh) * | 2015-07-27 | 2017-08-15 | 浙江京新药业股份有限公司 | 一种3‑[1‑(二甲基氨基)乙基]苯酚的制备方法 |
| CN105439906A (zh) * | 2015-12-08 | 2016-03-30 | 哈药集团三精制药有限公司 | 一种重酒石酸卡巴拉汀的合成方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS495325B1 (fr) * | 1965-09-29 | 1974-02-06 | ||
| IL74497A (en) * | 1985-03-05 | 1990-02-09 | Proterra Ag | Pharmaceutical compositions containing phenyl carbamate derivatives and certain phenyl carbamate derivatives |
| US4791107A (en) * | 1986-07-16 | 1988-12-13 | Hoechst-Roussel Pharmaceuticals, Inc. | Memory enhancing and analgesic 1,2,3,3A,8,8A-hexahydro-3A,8 (and) 1,3A,8)-di(and tri)methylpyrrolo(2,3-B)indoles, compositions and use |
| NL195004C (nl) * | 1987-03-04 | 2003-11-04 | Novartis Ag | Fenylcarbamaat bevattend farmaceutisch preparaat. |
| JPH07119189B2 (ja) * | 1989-09-28 | 1995-12-20 | 北陸製薬株式会社 | 光学活性なベンジルアルコール誘導体及びその用途 |
| SE8904064D0 (sv) * | 1989-12-01 | 1989-12-01 | Astra Ab | Improved method of preparing an intermediate for the manufacture of bambuterol |
| JP3705657B2 (ja) * | 1996-09-05 | 2005-10-12 | 信越化学工業株式会社 | Ｎ，ｎ−ジアルキルカルバミン酸２−ニトロベンジルエステル類の製造方法 |
| US6479495B1 (en) * | 1997-09-29 | 2002-11-12 | Aventis Pharmaceuticals Inc. | Aminoalkylphenol derivatives and related compounds |
| AU2001291077A1 (en) * | 2000-09-21 | 2002-04-02 | Teva Pharmaceuticals Industries Ltd. | N-disubstituted carbamoyloxy flavones |
| CZ20023555A3 (cs) * | 2002-10-24 | 2004-01-14 | Léčiva, A.S. | Způsob výroby (-)-(S)-3-[1-(dimethylamino)ethyl]fenyl-N-ethyl-N-methylkarbamátu |
| EP1689704A2 (fr) * | 2003-10-21 | 2006-08-16 | CoLucid Pharmaceuticals, Inc. | Esters de carbamoyle inhibant la cholinesterase et liberant des agents pharmacologiquement actifs |
| JP4954886B2 (ja) * | 2004-11-08 | 2012-06-20 | エムキュア ファーマシューティカルズ リミテッド | （ｓ）−３−［（１−ジメチルアミノ）エチル］−フェニル−ｎ−エチル−ｎ−メチル−カルバミン酸の効率的製造方法 |
-
2005
- 2005-10-29 JP JP2007539647A patent/JP4954886B2/ja not_active Expired - Fee Related
- 2005-10-29 WO PCT/IB2005/003237 patent/WO2006048720A1/fr active Application Filing
- 2005-10-29 ES ES05797945.2T patent/ES2615487T3/es active Active
- 2005-10-29 EP EP05797945.2A patent/EP1856036B1/fr not_active Not-in-force
- 2005-10-29 RU RU2007115398/04A patent/RU2393148C2/ru not_active IP Right Cessation
- 2005-10-29 KR KR1020077009495A patent/KR101168211B1/ko active IP Right Grant
-
2011
- 2011-11-28 JP JP2011259013A patent/JP2012072171A/ja active Pending
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